157929-17-4

Upstream product

• 583-55-1 1-Bromo-2-iodobenzene 
• 17573-94-3 4-ethynyl-N,N-dimethylaniline 

Downstream Products

• 1137270-43-9 N,N-dimethyl-4-(12-methylindolo[2,1-a]isoquinolin-6-yl)aniline 
• 1137270-55-3 N,N-dimethyl-(4-pyrrolo[2,1-a]isoquinolin-5-yl)aniline 
• 1151549-85-7 4-[2-[2-[2-[4-(dimethylamino)phenyl]ethynyl]phenyl]ethynyl]benzonitrile 
• 1396300-07-4 4-(10-methoxyindolo[2,1-a]isoquinolin-6-yl)-N,N-dimethylaniline 

Relevant academic research and scientific papers

Gold-catalyzed cycloisomerization of pyridine-bridged 1,8-diynes: An expedient access to luminescent cycl[3.2.2]azines

Gold-catalyzed diyne cycloisomerizations involving carbene/alkyne metathesis have been the focal point of attention for the past few years as it offers great potential to build complex polycyclic architectures. However, the design of novel cycloisomerizations has been mostly limited to 1,5/1,6-diynes and has remained very challenging to apply for higher 1,n-diynes. Herein, we disclose an unprecedented cycloisomerization of pyridine-bridged 1,8-diynes involving carbene/alkyne metathesis to access luminescent cycl[3.2.2]azines.

A new class of N-doped ionic PAHs: Via intramolecular [4+2]-cycloaddition between arylpyridines and alkynes

Reported herein, for the first time, is a copper-promoted intramolecular [4+2]-cycloaddition cascade to access ionic N-doped polycyclic aromatic hydrocarbons (PAHs) with tunable emission wavelengths. It is shown that the reaction can be made catalytic with respect to Cu(OTf)2 when an external oxidant, Selectfluor, was used.

Oxidative Intramolecular 1,2-Amino-Oxygenation of Alkynes under AuI/AuIIICatalysis: Discovery of a Pyridinium-Oxazole Dyad as an Ionic Fluorophore

Oxidative intramolecular 1,2-amino-oxygenation reactions, combining gold(I)/gold(III) catalysis, is reported. The reaction provides efficient access to a structurally unique ionic pyridinium-oxazole dyad with tunable emission wavelengths. The application of these fluorophores as potential biomarkers has been investigated.

Copper-catalyzed tandem synthesis of indolo-, pyrrolo[2,1-a]isoquinolines, naphthyridines and bisindolo/pyrrolo[2,1-a]isoquinolines via hydroamination of ortho-haloarylalkynes followed by C-2 arylation

An efficient approach for the copper-catalyzed regioselective tandem synthesis of diversely substituted indolo[2,1-a]isoquinolines 11a-r, pyrrolo[2,1-a]isoquinolines 12a-d, and indolo-, pyrrolo[2,1-f ][1,6]naphthyridines 14a-f via preferential addition of the heterocyclic amines onto the ortho-haloarylalkynes over N-arylation followed by intramolecular C-2 arylation is described. The scope of the developed chemistry was successfully extended for the direct synthesis of bisindolo-, pyrrolo[2,1-a]isoquinolines 15a-g, a regioisomer of the bisindolo[1,2-a]quinolines used as organic single-crystal field-effect transistor. Hydroxymethyl benzotriazole, which is an inexpensive and air stable compound, has been used as a ligand to carry out this onestep conversion of simple, readily available starting materials into an interesting class of heterocyclic compounds.

Di(1H-benzo[d][1,2,3]triazol-1-yl)methane: An efficient ligand for copper and amine-free palladium-catalysed Sonogashira coupling reaction

An efficient Pd-catalysed Sonogashira coupling reaction was achieved in the absence of copper and amine with inorganic base using phosphene-free, air stable di(1H-benzo[d][1,2,3]triazol-1-yl)methane as ligand. The cross coupling of electron-rich, electron-defficient and hindered aryl halides with terminal alkynes afforded the internal alkynes in good to excellent yields. Indian Academy of Sciences.

A copper-catalyzed tandem synthesis of indolo- and pyrrolo[2,1-a] isoquinolines

(Chemical Equation Presented) Isoquinoline ring the changes: A novel strategy for the title reaction involves ortho-haloarylalkynes which undergo sequential intermolecular addition of N heterocycles onto alkynes and subsequent intramolecular ring closure by arylation. The process involves the use of hydroxymethyl benzotriazole as an efficient and inexpensive ligand for the C - N and C - C coupling reactions.

Emission from regioisomeric bis(phenylethynyl)benzenes during pulse radiolysis

(Chemical Equation Presented) Emission from charge recombination between radical cations and anions of a series of regioisomeric 1,4-, 1,3-, and 1,2-bis(phenylethynyl)benzenes (bPEBs) substituted by various electron donor and/or acceptor groups was measured during pulse radiolysis in benzene (Bz). The formation of bPEB in the excited singlet state (1bPEB*) can be attributed to the charge recombination between bPEB?+ and bPEB?-, which are initially generated from the radiolytic reaction. This mechanism is reasonably explained by the relationship between the annihilation enthalpy change (-ΔH° ) for the charge recombination of bPEB?+ and bPEB?+ and excitation energy of 1bPEB*. Since the degree of the π-conjugation in the S 1 state and HOMO-LUMO levels of bPEB change with the substitution pattern of phenylacetylene groups on the central benzene ring and the various kinds of donor and/or acceptor group, the fine-tuning of the emission color and intensity of bPEB can be easily carried out during pulse radiolysis in Bz. For donor-acceptor-substituted bPEB, it was found that the difference in the charge transfer conjugated pathways between donor and acceptor substituents (linear-, cross-, and bent-conjugated pathways) strongly influenced the HOMO-LUMO energy gap.